Methanol → HCID 178499174、化合物

HRID 62082ノート

反応式

HRID 62082 の反応式
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([OH:12])=[O:11])=[N:2]1.[CH3:13]O>OS(O)(=O)=O>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]1

参加物

4

反応物 2

HCID 887MethanolHCID 1785249431H-pyrazolo[3,4-b]pyridine-3-carboxylic acid

生成物 1

HCID 178499174HCID 178499174、化合物収率 90%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid触媒

実験手順

To a solution of 1H-pyrazole[3,4-b]pyridine-3-carboxylic acid (V) (0.39 g, 2.4 mmol) in dry MeOH (10 mL) was added concentrated H2SO4 (4 drops) and refluxed for 6 h under nitrogen. The solution was cooled and the solvent was evaporated under vacuum. The residue was partitioned between DCM and saturated NaHCO3 solution. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified on a flash silica gel column (100% DCM→100:3 DCM:MeOH) to produce methyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate (VI) as a white solid (382 mg, 2.16 mmol, 90% yield). 1H NMR (CDCl3) δ ppm 4.08 (s, 3H), 7.38 (m, 1H), 8.63 (dd, J=8.10, 1.51 Hz, 1H), 8.72 (dd, J=4.62, 1.41 Hz, 1H); ESIMS found for C8H7N3O2 m/z 178.2 (M+H).

後処理

  1. temperaturerefluxed for 6 h under nitrogen
  2. temperatureThe solution was cooled
  3. customthe solvent was evaporated under vacuum
  4. customThe residue was partitioned between DCM and saturated NaHCO3 solution
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified on a flash silica gel column (100% DCM→100:3 DCM:MeOH)

出典と根拠

ORDレコード
ord-ff3eb8e8882d4f50972fb55ccd92e860
出典データセット
uspto-grants-2016_09
特許番号
US09446035B2

反応ノート

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